Esquire's Best Dressed Mobsters

A mobster's life ain't all it's made out to be, what with the rats, RICO laws, cops, and that little, last, nagging shred of your conscience that keeps telling you it wasn't cool to kill all those dudes just so you could hang out with a bunch of teamsters. But we'd be stool pigeons if we said a life of organized crime couldn't buy a guy some damn nice suits. And when you're a boss, no one can tell you how to wear what you wear, allowing crime kingpins to flex sartorially and break more than just the social contract. Here then, are the ten chicest mobsters according to Esquire.

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Joey Gallo

Bob Dylan doesn't write songs about just anyone, so you already knew Joey Gallo was one of the coolest mobsters just because your uncle who couldn't finish grad school and lived in your mom's basement had a copy of Desire sitting around. The guy was a born rebel, starting a mob war that ultimately got him killed (at Umberto's), but also breaking the staid rules of style left and right, like when he wore Ray-Ban Wayfarers and all black to testify before the U.S. Senate, where he told then Senator Robert Kennedy his office carpet would be perfect for a dice game.

Bugsy Siegel

A man doesn't pal around Hollywood starlets like Jean Harlow and go on to create modern Las Vegas with just regular old clothes on, and Bugsy Siegel was always dressed his best. The mobster's flashy lifestyle required flashy duds, which Siegel had in bundles, including favorites like his checked sport coat with wide lapels and a perfect three-roll-two button stance.

Cesare Bonventre

Cesare Bonventre wasn't a great mobster, but he was a great dresser. The Sicilian was the first to bring sprezzatura to Brooklyn, where he was fond of soft-shouldered Neapolitan suits, aviator glasses, and European-style men's handbags. Though he was most famous for selling out Carmine "Cigar" Gigante in a Bushwick restraint hit, before he himself was murdered in New Jersey, it's safe to call Bonventre the first #menswear don.

Joe Bonanno

You don't get the cover of Esquire by dressing like a scrub, and Joe Bonanno always looked fresh in his trademark fedora and double-breasted overcoat, menswear staples that are associated with mobsters to this day.

Lucky Luciano

Lucky Luciano was the father of modern organized crime. This winner of the Castellammarese War and founder of the infamous Commission dressed impeccably till his dying day, even wearing luxe smoking jackets and ties during his exile in Naples.

Joe Barboza

Joe "The Animal" Barboza was a goon and hit man, but the mob soldier and former professional boxer still kept his clothes looking sharp. Though he didn't always wear suits like some mentioned here, his more utilitarian look of sunglasses, cardigans, and chinos was perfectly suited to his work, and would inspired street thugs allover the East Coast, as can be seen on the Italian Jets in Westside Story.

Frank Costello

Luciano protégé and eventual boss of the Genovese crime family Frank Costello bore the nickname "Prime Minister of the Underworld," and he knew how to flex sartorially, but unlike a boring old politician, Costello did so in swaggering wide lapels and sprezzy pocket squares.

Meyer Lansky

Meyer Lansky actually was a criminal mastermind, founding the National Crime Syndicate, and doing so in sharp suits with subtly-roped shoulders, sunglasses, and bow ties. Neither the man, nor his looks were to be fked with, friends.

Al Capone

Al Capone owned Chicago and outsmarted the Feds for the better part of the 1920s before heading to Alcatraz on a tax evasion charge. He became the most infamous gangster of all time, and did so the whole time in three-piece suits and spats, while pioneering headwear staples like white fedoras